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metal-organic compounds
Bis(homopiperazinium) diaquapentakis(nitrato-κ2O,O′)lanthanate(III) dinitrate
aDepartment of Chemistry, University of Aberdeen, Meston Walk, Aberdeen AB24 3UE, Scotland
*Correspondence e-mail: w.harrison@abdn.ac.uk
The title compound, (C5H14N2)2[La(NO3)5(H2O)2](NO3)2, contains a network of doubly protonated homopiperazinium (1,4-diazoniacycloheptane) cations, diaquapentanitratolanthanate(III) dianions and nitrate anions. In the complex anion, the 12 O atoms surround La in a distorted icosahedral arrangement. A network of N—H⋯O and O—H⋯O hydrogen bonds help to consolidate the crystal packing, resulting in a three-dimensional network. The La atom and one N and one O atom lie on a twofold axis.
Comment
The title compound, (I) (Fig. 1
), contains organic dications, lanthanum/nitrate/water complex anions and non-coordinated nitrate anions. The LaIII cation, which occupies a twofold symmetry axis, is surrounded by five bidentate nitrate groups [mean La—O = 2.681 (2) Å] and two water molecules (Table 1
). The resulting O12 grouping (Fig. 2
) surrounding the La ion is a distorted icosahedron. As expected, the icosahedral O⋯O contacts associated with O atoms that are part of the same nitrate ion are much shorter (O⋯O < 2.17 Å) than the other contacts (O⋯O > 2.8 Å). Atoms O1, O5, O2i, O4i and O7i [symmetry code (i) −x, y,
− z] are approximately coplanar (r.m.s. deviation from the mean plane = 0.052 Å) and the symmetry-equivalent set of atoms O2, O4, O7, O1i and O5i have the same r.m.s. deviation. The La cation is displaced by 1.0046 (6) Å from each set of five O atoms. The dihedral angle between the two pentagons of O atoms is 1.42 (4)°. A very similar complex anion was seen in (CH6N3)2[La(H2O)2(NO3)5] (Fowkes & Harrison, 2004
).
The conformation of the homopiperazinium cation in (I) approximates to a chair, with atoms N1, C2, C3 and C5 almost coplanar (r.m.s. deviation from the mean plane = 0.033 Å) and C1, C4 and N2 displaced from the plane by −0.672 (3), 1.183 (3) and 1.028 (3) Å, respectively. A similar conformation for the same species was observed by Almond et al. (2000
) with the interesting difference that the `seat' of the chair was defined by four C atoms rather than three C atoms and one N atom as found here.
As well as coulombic and interact by way of O—H⋯O and N—H⋯O hydrogen bonds (Table 2
). The O9—H91⋯O1(x, 1 − y, z −
) bonds link adjacent [La(H2O)2(NO3)5]2− anions into infinite [100] chains (Fig. 3
) and the O9—H92⋯O12 bond attaches a pendant nitrate ion to the chain. The organic cations cross-link the chains into a three-dimensional network by way of the N—H⋯O interactions (Fig. 4
). In (CH6N3)2[La(H2O)2(NO3)5] (Fowkes & Harrison, 2004
), the anions form a two-dimensional hydrogen-bonded array, rather than the chains seen here.
![]() | Figure 1 Component units of (I) ![]() ![]() |
![]() | Figure 2 The LaO12 icosahedron in (I) ![]() ![]() |
![]() | Figure 3 Detail of a hydrogen-bonded anionic chain in (I) ![]() ![]() ![]() |
![]() | Figure 4 The packing in (I) ![]() ![]() |
Experimental
The following solutions were mixed at 293 K in a Petri dish to result in a clear solution: 5 ml of 0.1 M homopiperazine, 5 ml of 0.1 M lanthanum nitrate and 1 ml of 1 M HCl. Colourless blocks and slabs of (I) grew over the course of a few days as the water evaporated at 293 K.
Crystal data
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Refinement
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The water H atoms were located in a difference map and their positions were freely refined The other H atoms were placed in idealized locations [C—H = 0.97 Å and N—H = 0.90 Å] and refined as riding. The constraint Uiso(H) = 1.2Ueq(carrier atom) was applied in all cases.
Data collection: SMART (Bruker, 1999); cell SAINT-Plus (Bruker, 1999
); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997
); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997
); molecular graphics: ORTEP-3 (Farrugia, 1997
); software used to prepare material for publication: SHELXL97.
Supporting information
https://doi.org/10.1107/S1600536806017235/xu2043sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536806017235/xu2043Isup2.hkl
Data collection: SMART (Bruker, 1999); cell
SAINT-Plus (Bruker, 1999); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97.(C5H14N2)2[La(NO3)5(H2O)2](NO3)2 | F(000) = 1640 |
Mr = 813.38 | Dx = 1.876 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -C 2yc | Cell parameters from 9327 reflections |
a = 17.2458 (5) Å | θ = 2.0–32.5° |
b = 12.8660 (4) Å | µ = 1.60 mm−1 |
c = 13.4908 (4) Å | T = 293 K |
β = 105.780 (1)° | Slab, colourless |
V = 2880.59 (15) Å3 | 0.40 × 0.24 × 0.09 mm |
Z = 4 |
Bruker SMART 1000 CCD diffractometer | 5192 independent reflections |
Radiation source: fine-focus sealed tube | 4634 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.024 |
ω scans | θmax = 32.5°, θmin = 2.0° |
Absorption correction: multi-scan (SADABS; Bruker, 1999) | h = −26→26 |
Tmin = 0.568, Tmax = 0.870 | k = −19→14 |
16827 measured reflections | l = −20→20 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.025 | Hydrogen site location: difmap (O-H) and geom (others) |
wR(F2) = 0.062 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.00 | w = 1/[σ2(Fo2) + (0.0369P)2] where P = (Fo2 + 2Fc2)/3 |
5192 reflections | (Δ/σ)max = 0.002 |
211 parameters | Δρmax = 0.97 e Å−3 |
0 restraints | Δρmin = −0.79 e Å−3 |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
La1 | 0.0000 | 0.589697 (10) | 0.2500 | 0.01899 (4) | |
N4 | 0.14572 (9) | 0.53102 (13) | 0.43198 (12) | 0.0315 (3) | |
O1 | 0.07532 (8) | 0.50627 (11) | 0.43465 (10) | 0.0339 (3) | |
O2 | 0.15348 (8) | 0.56177 (12) | 0.34585 (10) | 0.0363 (3) | |
O3 | 0.20254 (10) | 0.52783 (16) | 0.50843 (13) | 0.0609 (5) | |
N5 | 0.09740 (10) | 0.78175 (12) | 0.35558 (11) | 0.0333 (3) | |
O4 | 0.08949 (9) | 0.76256 (11) | 0.26240 (9) | 0.0367 (3) | |
O5 | 0.06011 (8) | 0.72372 (10) | 0.40356 (9) | 0.0308 (3) | |
O6 | 0.13956 (15) | 0.85228 (16) | 0.40015 (13) | 0.0792 (7) | |
N6 | 0.0000 | 0.34742 (17) | 0.2500 | 0.0313 (4) | |
O7 | 0.05025 (9) | 0.39674 (10) | 0.21651 (12) | 0.0357 (3) | |
O8 | 0.0000 | 0.25002 (16) | 0.2500 | 0.0495 (6) | |
O9 | 0.08881 (8) | 0.60093 (11) | 0.12251 (9) | 0.0262 (2) | |
H91 | 0.0813 (13) | 0.5617 (18) | 0.0762 (18) | 0.031* | |
H92 | 0.0838 (13) | 0.6601 (19) | 0.0959 (17) | 0.031* | |
N1 | 0.09602 (10) | 0.18968 (13) | 0.10566 (12) | 0.0339 (3) | |
H1A | 0.0709 | 0.2210 | 0.1480 | 0.041* | |
H1B | 0.0757 | 0.2165 | 0.0423 | 0.041* | |
N2 | 0.23276 (10) | 0.11081 (14) | 0.30716 (13) | 0.0355 (4) | |
H2A | 0.2865 | 0.1013 | 0.3267 | 0.043* | |
H2B | 0.2164 | 0.1134 | 0.3650 | 0.043* | |
C1 | 0.07662 (14) | 0.07671 (17) | 0.10186 (16) | 0.0392 (4) | |
H1C | 0.1011 | 0.0430 | 0.0535 | 0.047* | |
H1D | 0.0187 | 0.0681 | 0.0763 | 0.047* | |
C2 | 0.10535 (12) | 0.02359 (17) | 0.20505 (16) | 0.0374 (4) | |
H2C | 0.0834 | −0.0463 | 0.1987 | 0.045* | |
H2D | 0.0835 | 0.0606 | 0.2540 | 0.045* | |
C3 | 0.19600 (12) | 0.01657 (16) | 0.24868 (16) | 0.0355 (4) | |
H3A | 0.2086 | −0.0433 | 0.2939 | 0.043* | |
H3B | 0.2202 | 0.0054 | 0.1925 | 0.043* | |
C4 | 0.21694 (13) | 0.21552 (16) | 0.25651 (15) | 0.0382 (4) | |
H4A | 0.2670 | 0.2543 | 0.2739 | 0.046* | |
H4B | 0.1794 | 0.2524 | 0.2859 | 0.046* | |
C5 | 0.18364 (12) | 0.21604 (16) | 0.14100 (15) | 0.0363 (4) | |
H5A | 0.1918 | 0.2844 | 0.1152 | 0.044* | |
H5B | 0.2135 | 0.1664 | 0.1117 | 0.044* | |
N7 | 0.12793 (11) | 0.80286 (16) | −0.01623 (13) | 0.0422 (4) | |
O10 | 0.1615 (2) | 0.7241 (2) | −0.0376 (2) | 0.1139 (12) | |
O11 | 0.13743 (14) | 0.88747 (15) | −0.05498 (17) | 0.0651 (6) | |
O12 | 0.08566 (15) | 0.79433 (16) | 0.04290 (19) | 0.0805 (7) |
U11 | U22 | U33 | U12 | U13 | U23 | |
La1 | 0.01944 (6) | 0.02038 (7) | 0.01708 (6) | 0.000 | 0.00484 (4) | 0.000 |
N4 | 0.0255 (7) | 0.0354 (9) | 0.0301 (7) | 0.0002 (6) | 0.0014 (5) | 0.0080 (6) |
O1 | 0.0279 (6) | 0.0412 (8) | 0.0323 (6) | −0.0002 (6) | 0.0075 (5) | 0.0128 (6) |
O2 | 0.0271 (6) | 0.0510 (9) | 0.0319 (6) | 0.0004 (6) | 0.0100 (5) | 0.0086 (6) |
O3 | 0.0400 (9) | 0.0812 (14) | 0.0452 (9) | −0.0110 (9) | −0.0161 (7) | 0.0229 (9) |
N5 | 0.0442 (9) | 0.0305 (8) | 0.0249 (6) | −0.0137 (7) | 0.0090 (6) | −0.0031 (6) |
O4 | 0.0540 (8) | 0.0357 (7) | 0.0226 (5) | −0.0117 (6) | 0.0141 (5) | −0.0023 (5) |
O5 | 0.0385 (7) | 0.0318 (7) | 0.0242 (5) | −0.0106 (6) | 0.0121 (5) | −0.0038 (5) |
O6 | 0.1314 (19) | 0.0706 (13) | 0.0381 (8) | −0.0730 (14) | 0.0272 (10) | −0.0199 (9) |
N6 | 0.0340 (11) | 0.0245 (10) | 0.0379 (11) | 0.000 | 0.0140 (9) | 0.000 |
O7 | 0.0358 (7) | 0.0296 (7) | 0.0473 (8) | 0.0002 (5) | 0.0211 (6) | 0.0054 (6) |
O8 | 0.0635 (14) | 0.0211 (10) | 0.0784 (16) | 0.000 | 0.0440 (13) | 0.000 |
O9 | 0.0293 (6) | 0.0295 (7) | 0.0214 (5) | 0.0000 (5) | 0.0096 (5) | −0.0027 (5) |
N1 | 0.0394 (8) | 0.0374 (9) | 0.0239 (6) | 0.0124 (7) | 0.0065 (6) | 0.0044 (6) |
N2 | 0.0260 (7) | 0.0480 (10) | 0.0300 (7) | 0.0019 (7) | 0.0034 (6) | 0.0098 (7) |
C1 | 0.0393 (10) | 0.0423 (12) | 0.0312 (9) | 0.0004 (8) | 0.0013 (8) | −0.0025 (8) |
C2 | 0.0345 (9) | 0.0384 (11) | 0.0384 (9) | −0.0047 (8) | 0.0083 (8) | 0.0056 (8) |
C3 | 0.0348 (9) | 0.0326 (10) | 0.0404 (9) | 0.0067 (8) | 0.0124 (8) | 0.0113 (8) |
C4 | 0.0376 (10) | 0.0359 (11) | 0.0374 (9) | −0.0026 (8) | 0.0037 (8) | 0.0022 (8) |
C5 | 0.0391 (10) | 0.0356 (10) | 0.0370 (9) | 0.0029 (8) | 0.0153 (8) | 0.0101 (8) |
N7 | 0.0451 (9) | 0.0487 (11) | 0.0360 (8) | 0.0017 (8) | 0.0167 (7) | 0.0105 (8) |
O10 | 0.174 (3) | 0.0730 (17) | 0.140 (3) | 0.0222 (18) | 0.119 (2) | 0.0206 (16) |
O11 | 0.0918 (15) | 0.0487 (10) | 0.0728 (13) | 0.0027 (10) | 0.0528 (12) | 0.0167 (9) |
O12 | 0.1119 (17) | 0.0625 (13) | 0.0973 (16) | 0.0236 (12) | 0.0797 (15) | 0.0343 (11) |
La1—O1i | 2.6990 (12) | N1—C5 | 1.495 (3) |
La1—O1 | 2.6990 (12) | N1—H1A | 0.9000 |
La1—O2i | 2.6355 (13) | N1—H1B | 0.9000 |
La1—O2 | 2.6355 (13) | N2—C3 | 1.491 (3) |
La1—O4 | 2.6863 (14) | N2—C4 | 1.502 (3) |
La1—O4i | 2.6863 (14) | N2—H2A | 0.9000 |
La1—O5 | 2.6780 (12) | N2—H2B | 0.9000 |
La1—O5i | 2.6780 (12) | C1—C2 | 1.508 (3) |
La1—O7i | 2.7076 (13) | C1—H1C | 0.9700 |
La1—O7 | 2.7076 (13) | C1—H1D | 0.9700 |
La1—O9i | 2.5996 (12) | C2—C3 | 1.516 (3) |
La1—O9 | 2.5996 (12) | C2—H2C | 0.9700 |
N4—O3 | 1.215 (2) | C2—H2D | 0.9700 |
N4—O1 | 1.2651 (19) | C3—H3A | 0.9700 |
N4—O2 | 1.2686 (19) | C3—H3B | 0.9700 |
N5—O6 | 1.215 (2) | C4—C5 | 1.507 (3) |
N5—O4 | 1.2516 (18) | C4—H4A | 0.9700 |
N5—O5 | 1.2713 (18) | C4—H4B | 0.9700 |
N6—O8 | 1.253 (3) | C5—H5A | 0.9700 |
N6—O7 | 1.2533 (17) | C5—H5B | 0.9700 |
N6—O7i | 1.2532 (17) | N7—O12 | 1.223 (2) |
O9—H91 | 0.79 (2) | N7—O11 | 1.238 (2) |
O9—H92 | 0.84 (2) | N7—O10 | 1.238 (3) |
N1—C1 | 1.489 (3) | ||
O9i—La1—O9 | 173.63 (6) | O1—La1—O7 | 72.17 (5) |
O9i—La1—O2i | 68.80 (4) | O7i—La1—O7 | 47.05 (6) |
O9—La1—O2i | 112.14 (4) | O3—N4—O1 | 121.74 (16) |
O9i—La1—O2 | 112.14 (4) | O3—N4—O2 | 121.77 (17) |
O9—La1—O2 | 68.80 (4) | O1—N4—O2 | 116.47 (14) |
O2i—La1—O2 | 164.33 (7) | N4—O1—La1 | 95.65 (9) |
O9i—La1—O5 | 68.05 (4) | N4—O2—La1 | 98.62 (10) |
O9—La1—O5 | 107.59 (4) | O6—N5—O4 | 122.11 (16) |
O2i—La1—O5 | 126.38 (4) | O6—N5—O5 | 120.28 (15) |
O2—La1—O5 | 65.32 (4) | O4—N5—O5 | 117.61 (14) |
O9i—La1—O5i | 107.59 (4) | N5—O4—La1 | 97.45 (10) |
O9—La1—O5i | 68.05 (4) | N5—O5—La1 | 97.31 (9) |
O2i—La1—O5i | 65.32 (4) | O8—N6—O7 | 120.42 (11) |
O2—La1—O5i | 126.38 (4) | O8—N6—O7i | 120.42 (11) |
O5—La1—O5i | 99.83 (6) | O7—N6—O7i | 119.2 (2) |
O9i—La1—O4 | 110.16 (4) | N6—O7—La1 | 96.89 (11) |
O9—La1—O4 | 64.10 (4) | La1—O9—H91 | 119.4 (17) |
O2i—La1—O4 | 128.81 (5) | La1—O9—H92 | 108.9 (15) |
O2—La1—O4 | 66.36 (5) | H91—O9—H92 | 106 (2) |
O5—La1—O4 | 47.45 (4) | C1—N1—C5 | 115.51 (16) |
O5i—La1—O4 | 67.05 (4) | C1—N1—H1A | 108.4 |
O9i—La1—O4i | 64.10 (4) | C5—N1—H1A | 108.4 |
O9—La1—O4i | 110.16 (4) | C1—N1—H1B | 108.4 |
O2i—La1—O4i | 66.36 (5) | C5—N1—H1B | 108.4 |
O2—La1—O4i | 128.81 (5) | H1A—N1—H1B | 107.5 |
O5—La1—O4i | 67.05 (4) | C3—N2—C4 | 119.36 (15) |
O5i—La1—O4i | 47.45 (4) | C3—N2—H2A | 107.5 |
O4—La1—O4i | 68.22 (6) | C4—N2—H2A | 107.5 |
O9i—La1—O1i | 114.24 (4) | C3—N2—H2B | 107.5 |
O9—La1—O1i | 68.51 (4) | C4—N2—H2B | 107.5 |
O2i—La1—O1i | 47.62 (4) | H2A—N2—H2B | 107.0 |
O2—La1—O1i | 124.45 (4) | N1—C1—C2 | 113.34 (16) |
O5—La1—O1i | 163.32 (5) | N1—C1—H1C | 108.9 |
O5i—La1—O1i | 63.53 (4) | C2—C1—H1C | 108.9 |
O4—La1—O1i | 120.72 (4) | N1—C1—H1D | 108.9 |
O4i—La1—O1i | 98.49 (4) | C2—C1—H1D | 108.9 |
O9i—La1—O1 | 68.51 (4) | H1C—C1—H1D | 107.7 |
O9—La1—O1 | 114.24 (4) | C1—C2—C3 | 115.50 (17) |
O2i—La1—O1 | 124.45 (4) | C1—C2—H2C | 108.4 |
O2—La1—O1 | 47.62 (4) | C3—C2—H2C | 108.4 |
O5—La1—O1 | 63.53 (4) | C1—C2—H2D | 108.4 |
O5i—La1—O1 | 163.32 (5) | C3—C2—H2D | 108.4 |
O4—La1—O1 | 98.49 (4) | H2C—C2—H2D | 107.5 |
O4i—La1—O1 | 120.72 (4) | N2—C3—C2 | 113.72 (16) |
O1i—La1—O1 | 133.13 (6) | N2—C3—H3A | 108.8 |
O9i—La1—O7i | 70.59 (4) | C2—C3—H3A | 108.8 |
O9—La1—O7i | 115.74 (4) | N2—C3—H3B | 108.8 |
O2i—La1—O7i | 68.44 (5) | C2—C3—H3B | 108.8 |
O2—La1—O7i | 96.75 (5) | H3A—C3—H3B | 107.7 |
O5—La1—O7i | 122.37 (4) | N2—C4—C5 | 116.45 (17) |
O5i—La1—O7i | 130.19 (5) | N2—C4—H4A | 108.2 |
O4—La1—O7i | 162.41 (5) | C5—C4—H4A | 108.2 |
O4i—La1—O7i | 124.40 (4) | N2—C4—H4B | 108.2 |
O1i—La1—O7i | 72.17 (5) | C5—C4—H4B | 108.2 |
O1—La1—O7i | 64.97 (5) | H4A—C4—H4B | 107.3 |
O9i—La1—O7 | 115.74 (4) | N1—C5—C4 | 113.38 (15) |
O9—La1—O7 | 70.59 (4) | N1—C5—H5A | 108.9 |
O2i—La1—O7 | 96.75 (5) | C4—C5—H5A | 108.9 |
O2—La1—O7 | 68.44 (5) | N1—C5—H5B | 108.9 |
O5—La1—O7 | 130.19 (5) | C4—C5—H5B | 108.9 |
O5i—La1—O7 | 122.37 (4) | H5A—C5—H5B | 107.7 |
O4—La1—O7 | 124.40 (4) | O12—N7—O11 | 121.7 (2) |
O4i—La1—O7 | 162.41 (5) | O12—N7—O10 | 118.5 (2) |
O1i—La1—O7 | 64.97 (5) | O11—N7—O10 | 119.8 (2) |
O3—N4—O1—La1 | 165.63 (19) | O1—La1—O4—N5 | −39.07 (12) |
O2—N4—O1—La1 | −12.69 (18) | O7i—La1—O4—N5 | −58.18 (19) |
O9i—La1—O1—N4 | −147.79 (12) | O7—La1—O4—N5 | −113.23 (12) |
O9—La1—O1—N4 | 25.97 (12) | O6—N5—O5—La1 | −175.0 (2) |
O2i—La1—O1—N4 | 170.05 (10) | O4—N5—O5—La1 | 4.27 (18) |
O2—La1—O1—N4 | 7.36 (10) | O9i—La1—O5—N5 | −153.38 (12) |
O5—La1—O1—N4 | −72.44 (11) | O9—La1—O5—N5 | 21.68 (11) |
O5i—La1—O1—N4 | −68.28 (18) | O2i—La1—O5—N5 | −114.76 (11) |
O4—La1—O1—N4 | −39.39 (12) | O2—La1—O5—N5 | 77.40 (11) |
O4i—La1—O1—N4 | −109.04 (11) | O5i—La1—O5—N5 | −48.26 (10) |
O1i—La1—O1—N4 | 108.57 (11) | O4—La1—O5—N5 | −2.39 (10) |
O7i—La1—O1—N4 | 134.35 (12) | O4i—La1—O5—N5 | −83.30 (11) |
O7—La1—O1—N4 | 84.12 (11) | O1i—La1—O5—N5 | −52.03 (19) |
O3—N4—O2—La1 | −165.23 (18) | O1—La1—O5—N5 | 130.53 (11) |
O1—N4—O2—La1 | 13.09 (18) | O7i—La1—O5—N5 | 159.45 (10) |
O9i—La1—O2—N4 | 17.58 (13) | O7—La1—O5—N5 | 100.81 (11) |
O9—La1—O2—N4 | −169.21 (13) | O8—N6—O7—La1 | 180.0 |
O2i—La1—O2—N4 | −72.69 (11) | O7i—N6—O7—La1 | 0.0 |
O5—La1—O2—N4 | 68.44 (11) | O9i—La1—O7—N6 | 17.68 (10) |
O5i—La1—O2—N4 | 152.40 (11) | O9—La1—O7—N6 | −163.14 (10) |
O4—La1—O2—N4 | 120.76 (12) | O2i—La1—O7—N6 | −52.00 (9) |
O4i—La1—O2—N4 | 91.44 (12) | O2—La1—O7—N6 | 122.71 (9) |
O1i—La1—O2—N4 | −127.15 (11) | O5—La1—O7—N6 | 99.86 (8) |
O1—La1—O2—N4 | −7.39 (10) | O5i—La1—O7—N6 | −116.98 (8) |
O7i—La1—O2—N4 | −54.17 (12) | O4—La1—O7—N6 | 160.22 (7) |
O7—La1—O2—N4 | −92.51 (12) | O4i—La1—O7—N6 | −67.52 (17) |
O6—N5—O4—La1 | 175.0 (2) | O1i—La1—O7—N6 | −88.45 (9) |
O5—N5—O4—La1 | −4.26 (18) | O1—La1—O7—N6 | 72.07 (8) |
O9i—La1—O4—N5 | 31.07 (12) | O7i—La1—O7—N6 | 0.0 |
O9—La1—O4—N5 | −151.96 (13) | C1—C2—C3—N2 | 85.3 (2) |
O2i—La1—O4—N5 | 109.59 (11) | C2—C3—N2—C4 | −54.1 (2) |
O2—La1—O4—N5 | −75.04 (11) | C3—N2—C4—C5 | −16.1 (3) |
O5—La1—O4—N5 | 2.43 (10) | N2—C4—C5—N1 | 76.5 (2) |
O5i—La1—O4—N5 | 132.26 (12) | C4—C5—N1—C1 | −81.6 (2) |
O4i—La1—O4—N5 | 80.70 (11) | C5—N1—C1—C2 | 60.2 (2) |
O1i—La1—O4—N5 | 167.69 (10) | N1—C1—C2—C3 | −67.0 (2) |
Symmetry code: (i) −x, y, −z+1/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
O9—H91···O1ii | 0.79 (2) | 2.08 (2) | 2.8388 (17) | 163 (2) |
O9—H92···O12 | 0.84 (2) | 1.87 (2) | 2.705 (2) | 173 (2) |
N1—H1A···O8 | 0.90 | 2.11 | 2.9817 (17) | 163 |
N1—H1B···O5ii | 0.90 | 1.97 | 2.8531 (19) | 165 |
N2—H2A···O9iii | 0.90 | 2.07 | 2.966 (2) | 172 |
N2—H2B···O11iv | 0.90 | 1.95 | 2.797 (2) | 155 |
Symmetry codes: (ii) x, −y+1, z−1/2; (iii) −x+1/2, y−1/2, −z+1/2; (iv) x, −y+1, z+1/2. |
Acknowledgements
AF thanks the Carnegie Trust for the Universities of Scotland for a vacation scholarship.
References
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